The 3 Best Lessons I Learned From Talking About My Work Insecurities With My Boss

I recently ran into a bit of a snag on a project I was working on. And no matter what I tried, it just felt like I was never going to get it right. So, after staring at the same document for a couple of days, I did something I never thought I’d do: I told my boss I was having a hard time and opened up about how insecure this made me feel. At first, I immediately regretted approaching her. After all, she’s my boss, and not only do I respect and admire her, I was afraid of looking completely lost in front of her. But, when she gave me the exact confidence boost I needed, I ended up learning some valuable lessons about admitting that I wasn’t feeling my best.

1. Not Getting Something Right the First Time Doesn’t Make You Bad at Your Job

I tend to be hard on myself, even though as a full-time writer, I know that very few people write first drafts that are just so good, their editors say, “This is incredible, let’s just run it!” However, it’s totally understandable for people in any line of work to feel like they’re just the worst because their first pass at something didn’t go as planned. Of course, this isn’t something I’m typically good at understanding, because like everyone else, I dream of being the exception. But here’s what I have to remember: Sometimes my first drafts are strong, and other times, they’re just a little more challenging than anticipated. But, that doesn’t make me bad at my job. And it doesn’t make you bad at yours, either.

2. Admitting You Need Help Makes You a Better Teammate

I’m fortunate enough to work with some insanely smart people on a daily basis, so I put a lot of pressure on myself to get things done without much help. And although my mother would probably approve of this mindset to a certain extent, there’s one serious flaw with this kind of thinking. If you don’t understand something, you actually could be holding back your team from getting something critical done.

What’s worse, nobody’s going to know how much you’re struggling if you don’t speak up for yourself. So, when I fessed up to my boss about how down I was feeling, not only did I get the confidence boost I needed, I also got the chance to talk the project out with her. And ultimately, we realized it was a project that required more thought, would take more time, and require me to ask a few other people some additional questions. All good things, right? From where I’m sitting, they’re all things I would have never realized if I hadn’t gotten up the courage to admit I was stuck.

3. Even the Most Experienced People Need a Little Encouragement

The more people I talk to about this whole thing, the more that I realize that some of the most talented people I know run into this problem, too. While it was a little bit of a shock to me at first, it makes perfect sense. Because who on the face of this earth knows what they’re doing 100% of the time. And how many people, no matter how smart they are, have gone their entire lives without asking for a little bit of help?

Sure, there are plenty of people out there who haven’t asked outright for a bit of a confidence boost, but I’d wager that nobody you know has done his or her job without asking for assistance at one point or another. Sometimes when you’re working hard, you hit a wall. And when you hit that wall, it’s perfectly OK to ask for a few words of encouragement, even if you’re the best at whatever it is you do for a living.

I’m sure there are plenty of people who would still feel uneasy about going up to a boss or colleague and saying, “Hey, this project’s making me feel like an idiot. Can you remind me why I was chosen to lead it?” And I’ll admit that it still makes me uncomfortable, especially since I still haven’t figured out how to stop beating myself up when I don’t do something perfectly. But, every time I’ve asked for a little help, I remembered that saying those words aloud doesn’t cause the world to collapse.

And when I asked for a little bit of a pep talk from my boss recently, I didn’t get fired or lose her trust. If anything, I became a little better at my job in ways I wouldn’t have if I hadn’t spoken up about how I was feeling a little lost. So, next time you need that confidence boost, think about straight up asking for it. And, taking this concept a little further, the next time you see a colleague struggling give him or her a few words of encouragement yourself.

Richard Moy is a Content Marketing Writer at Stack Overflow. He has spent the majority of his career in talent management, including a stint as a full-cycle recruiter and hiring manager. In addition to the career advice he contributes to The Muse, he also writes test prep and higher education marketing content for The Economist. Say hi on Twitter @rich_moy.

Meet The Author

Richard Moy is a Content Marketing Writer at Stack Overflow. He has spent the majority of his career in talent management, including a stint as a full-cycle recruiter and hiring manager. In addition to the career advice he contributes to The Muse, he also writes test prep and higher education marketing content for The Economist. Say hi on Twitter @rich_moy.